The American Bankers’ Association (ABA) was faced with the challenge of raising the technology literacy of its staff to maintain its competitive advantage as a world-class solution provider for its members. It developed a 90 Day “Learn 50 New Things” campaign which involved a series of technology ‘tip sessions,’ brown-bag lunches, and one-on-one user sessions, among other activities. It offered various prizes to those who achieved the target of learning 50 new helpful hardware and software features that could be incorporated into daily work. The resulting initiative achieved a nearly 80% participation rate, with high rates of general and department-specific technological skill acquisition achieved and nearly 20% rise in both the rate web technology usage and employee technology confidence.